(Z)-9-Tricosene

(Z)-9-Tricosene

Names
IUPAC name (9Z)-9-Tricosene
Other names Muscalure[1]
Identifiers
CAS Number	27519-02-4
ChemSpider	4517167
Jmol 3D model	Interactive image
PubChem	5365075
InChI InChI=1S/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17- Key: IGOWHGRNPLFNDJ-ZPHPHTNESA-N InChI=1/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17- Key: IGOWHGRNPLFNDJ-ZPHPHTNEBA
SMILES C(=C\CCCCCCCCCCCCC)\CCCCCCCC
Properties
Chemical formula	C23H46
Molar mass	322.62 g·mol^−1
Density	0.806 g/mL[2]
Boiling point	300 °C (572 °F; 573 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

(Z)-9-Tricosene (muscalure) is an insect pheromone used as a pesticide.

Biological functions

(Z)-9-Tricosene is a sex pheromone produced by female house flies (Musca domestica) to attract males. In bees, it is one of the communication pheromones released during the waggle dance.^[3]

Uses

As a pesticide, (Z)-9-tricosene is used in fly paper and other traps to lure male flies, trap them, and prevent them from reproducing.^[4]

Biosynthesis

(Z)-9-Tricosene is biosynthesized in house flies from nervonic acid.^[5] The acid is converted into the acyl-CoA derivative and then reduced to the aldehyde (Z)-15-tetracosenal. Through a decarboxylation reaction, the aldehyde is converted to (Z)-9-tricosene. The process is mediated by a cytochrome P450 enzyme and requires oxygen (O₂) and nicotinamide adenine dinucleotide phosphate (NADPH).

Biosynthesis of (Z)-9-tricosene (bottom) from nervonic acid (top)

Safety

Products containing (Z)-9-tricosene are considered safe for humans, wildlife, and the environment.^[4]

References

1. "Muscalure". alanwood.net.
2. "(Z)-9-Tricosene". Sigma-Aldrich.
3. Thom, C.; Gilley, D.; Hooper, J.; Esch, H. (2007). "The scent of the waggle dance". PLoS Biology 5 (9): e228. doi:10.1371/journal.pbio.0050228. PMC 1994260. PMID 17713987.
4. "(Z)-9-Tricosene (103201) Fact Sheet". United States Environmental Protection Agency.
5. Reed, JR; Vanderwel, D; Choi, S; Pomonis, JG; Reitz, RC; Blomquist, GJ (1994). "Unusual mechanism of hydrocarbon formation in the housefly: Cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2" (PDF). Proceedings of the National Academy of Sciences of the United States of America 91 (21): 10000–4. doi:10.1073/pnas.91.21.10000. PMC 44945. PMID 7937826.